Leading (Digital) Transformation From the Inside Out

Change is constant, and going faster than ever. We call it innovation, transformation and continuous improvement. It happens with success, failure, acquisitions and mergers. We can manage the change, or the change will manage—and likely defeat—us. And, if you are reading this column, you like to win.

Last month, I wrote about the how best people to lead your business/digital transformation might be right under your roof. She or he knows the fabric, the culture, the fears and doubts, the org chart as well as the power map. And they have the informal network to get things discussed, debated and done. It takes a team—indeed, usually many teams—to truly succeed.

Transformation is not easy. It takes work, skills and patience. Skillsets and mindsets and tool kits are likely new and different to be successful. Here are some we have seen in our 30 years in the change field – and the last five to 10 in digital transformation.

Have a clear purpose. Know the “why” of the transformation. Yes, there is always the strategic plan—and the purpose of that strategy has to be simple and clear. The leaders of your transformation must understand the “why” deeply in his/her bones—and believe in it.

Meet them where they are. It does not work to have a clear vision and plan if it seems unrealistic, impossible and irrelevant to your people. The great leaders of change have empathy—they know how to connect to the different groups in the business and speak their language, empathize with their circumstances, and their doubts and pains.

Communicate, communicate, communicate. Said another way: share, listen and learn. Effective communication is really not that easy. It means that your leader(s) need to be able to articulate the proposition well, and what is expected—and in the language of the existing culture and mindset of your people (as above). They need to listen to the fears and doubts, challenges and ideas of the people who will have to inform, learn, execute and live with the change (or not). And they need to know you’ve heard them—you’ve learned from them. Keep the dialogue alive, being responsive and engaged.

Accept and embrace failure. Failure is a learning opportunity. Almost all success—even those considered “overnight”—in truth were years of failure (or limited success) in the making. The tools of rapid transformation are no longer top-down. Success never has been a straight path, no matter how neat and clean your plan looks on paper. It is organic, iterative, interactive and fast.  Your leaders need to be able to accept and learn from the failures, and then help others to do the same.

When you have a culture and leaders that have these attributes, then your insider-leader can help your external and new-hire experts be accepted and embraced, and the transformation can truly deliver spectacular results.♦

Stephen Garber is director of Third Level Ltd. Contact him at 561.752.5505 or [email protected].

You May Also Like
A collage of downtown Fort Lauderdale features skyscrapers, a convention center, port with shipping containers, an airplane overhead, two workers in hard hats, a handshake at a business event, and a Las Olas Blvd street sign. South Florida Business & Wealth
Broward Business Momentum
January 30, 2026
A luxurious waterfront home with palm trees, a large dock, and two white boats moored on a calm canal under a clear blue sky at sunset. South Florida Business & Wealth
Docked by the Rules
January 29, 2026
A serene outdoor pool with lounge chairs and towels, surrounded by lush greenery, in front of a modern building with balconies and large glass doors leading to a well-lit interior. South Florida Business & Wealth
Downtown cityscape of Broward at sunset with high-rise buildings, palm trees, and blurred car lights. Text overlay reads: "Broward Business Pulse: Five Signals Shaping the Week. South Florida Business & Wealth
Broward Business Pulse
January 25, 2026
Breaking the Glass Ceiling in Senior Living

Melissa Honig becomes the first woman CEO in John Knox Village’s history, signaling a thoughtful evolution in Florida senior living.

Read More
A woman with long, straight blonde hair smiles broadly at the camera. She is wearing a sleeveless pink and white top and is posed in front of a plain, light-colored background. South Florida Business & Wealth
Where the Money Still Says “Yes”

In Fort Lauderdale and beyond, lenders and buyers are voting for proven assets, strong locations, and real demand.

Read More
Aerial view of a waterfront cityscape with tall modern buildings, a large hotel or convention center, palm trees, and several yachts docked along a marina under a partly cloudy sky. South Florida Business & Wealth
Rewriting the Blueprint

From development and design to brokerage and urban planning, these women are changing not just skylines, but the culture behind them.

Read More
Blueprint-style illustration featuring silhouettes of five women holding blueprints, standing in front of a cityscape and architectural plans, with the text “The Women Rewriting The Blueprint” prominently displayed above. South Florida Business & Wealth
Radence Plants Its Flag in West Palm Beach

The precision health company selects South Florida for its flagship hub, underscoring the region’s rising influence in healthcare innovation.

Read More
Skyline of West Palm Beach at sunset with modern buildings reflected in the water. Text reads: "Radence Chooses West Palm Beach for Flagship Hub—Boosting South Florida’s Role in Healthcare and Technology Innovation. South Florida Business & Wealth
Other Posts
PEBB Enterprises Sells Cypress Creek Office Asset for $11.93 Million

Longtime owner exits the 6400 Building as it sharpens focus on new South Florida office opportunities

Read More
Memorial’s Recent Moves

Rita Bunch added to Hospital’s Leadership Team

Read More
A woman with wavy, light brown hair smiles at the camera. She is wearing a dark-colored blazer and a light-colored blouse. The background is a soft blue gradient. South Florida Business & Wealth
A Quiet Week, Not a Slow One

Broward’s Latest Business Moves— and What’s Coming

Read More
A charming street with outdoor café seating, tables and chairs lined up, shopfronts with awnings, and string lights; text reads "Broward’s Latest Business Moves. A look at the announcements that actually mattered this week. South Florida Business & Wealth
Why Billionaire Migration Matters to South Florida’s Economy

From real estate to financial services, the impact of wealth relocation is becoming increasingly local.

Read More
Two men in business suits stand in front of a backdrop featuring a city skyline with tall buildings, water, and luxury waterfront homes surrounded by palm trees, under a clear blue sky. South Florida Business & Wealth